HCID 21071776, compound → 7-Bromo-5-methyl-1-benzofuran

HRID 1372165Notes

Reaction equation

HRID 1372165 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:10][CH:11](OC)OC>ClC1C=CC=CC=1>[Br:1][C:2]1[C:3]2[O:9][CH:10]=[CH:11][C:4]=2[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

3

Reactant 1

HCID 21071776HCID 21071776, compound

Product 1

HCID 210718017-Bromo-5-methyl-1-benzofuranYield 66%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Procedure

To a 2 L round bottom flask was added PPA (3 g), anhydrous chlorobenzene (1.0 L) and the mixture was brought to reflux followed by the slow addition of 2-bromo-1-(2,2-dimethyoxy-ethoxy)-4-methyl benzene (22.9 g, 83.3 mmol) in chlorobenzene (200 ml) by addition funnel over a 2 h period. The reaction was then cooled and passed through a silica plug (washed with chlorobenzene) and concentrated to a mixture of product plus 4-iodo-2-methylphenol. Column chromatography (10% EtOAc/hexane) afforded 11.54 g (66%) of product as a clear oil: 1H NMR (300 MHz, DMSO-d6): δ 2.40 (3H, s), 7.02 (1H, d, J=2.2 Hz), 7.39 (1H, s), 7.45 (1H, s), 8.07 (1H, d, J=2.2 Hz).

Workup

  1. temperatureto reflux
  2. temperatureThe reaction was then cooled
  3. concentrationconcentrated to a mixture of product plus 4-iodo-2-methylphenol

Sources & evidence

ORD record
ord-301436509b474da3ba0657288b6fe67d
Source dataset
uspto-grants-2007_01
Patent number
US07157491B2

Reaction notes

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